1. Field of the Invention
This invention relates to novel 5-aroyl-6-alkylthio, 6-alkylsulfinyl and 6-alkylsulfonyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acids and the pharmaceutically acceptable, non-toxic esters and salts thereof. The invention also relates to the intermediates necessary for the preparation of these compounds and to the processes for preparing the compounds of this invention. It further relates to the use of these compounds as anti-inflammatory agents, analgesic agents, antipyretic agents, platelet aggregation inhibitors, fibrinolytic agents and smooth muscle relaxants. The use of these compounds is both prophylactic and therapeutic. This invention still further relates to the pharmaceutical compositions comprising a compound of this invention and at least one pharmaceutical excipient.
2. Related Disclosures
Compounds which are structurally related to the instant invention are those which are represented by the formula ##STR2## wherein P is a moiety selected from the group consisting of ##STR3## in which
X is oxygen or sulfur,
R is hydrogen, methyl, chloro or bromo, the R substitution being at the 3, 4 or 5 positions of the heterocyclic ring,
R.sup.1 is hydrogen, a lower alkyl group having 1 to 4 carbon atoms, a lower alkoxy group having from 1 to 4 carbon atoms, chloro, fluoro or bromo, the R.sup.1 substitution being at the ortho, meta or para positions of the phenyl group, and
R.sup.2 and R.sup.3 are each independently hydrogen or a lower alkyl group having from 1 to 4 carbon atoms.
The compounds represented by Formula (IA) and (ID) are disclosed in U.S. Pat. No. 4,087,539, issued May 2, 1978 to Muchowski et al, while compounds of Formulas (IB) and (IC) are disclosed in U.S. Pat. Nos. 4,089,969, issued May 16, 1978 to Muchowski et al and U.S. Pat. No. 4,097,579 issued June 27, 1978 to Muchowski et al, respectively.
Compounds of Formula (IB) wherein R.sup.1 is methylthio are disclosed in co-pending U.S. application No. 71,444 filed Aug. 31, 1979, now abandoned, and compounds wherein R.sup.1 is methylsulfinyl or methylsulfonyl are disclosed in U.S. Pat. No. 4,232,038, issued Nov. 4, 1980. All of these compounds are useful as anti-inflammatory agents, analgesic agents, platelet aggregation inhibitors, fibrinolytic agents and smooth muscle relaxants. They can be used both prophylactically and therapeutically.